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Is your cubicle caving in on you? Maybe it’s time to become your own boss. Just take it from these self-employed women who are already “living the dream”: They work, play and slay on their own terms. Their advice might just be the final motivation you need to put in your notice.

You Call The Shots
Caitlin McAllister – Desk Life Project

“In the beginning, I had just left a well-paid job to work freelance, so I was saying yes to anything, fearful that I might lose out on an opportunity. A friend told me to remember that it’s my business, and I get to call the shots, which I really needed to hear. It’s good to keep in mind that you went freelance for a reason, and now you get to decide when you work, who you work with and what you work on. That means charging what you believe your work is worth, and running your own calendar to make time for what you love.

“I think the idea of success is very objective, and it can sometimes sneak up on you. I’ve found that being consistent in showing up for your goal means that eventually opportunities will arise, you will start to meet the right people, and things will begin to fall into place. Don’t underestimate the power of having patience and a quiet drive to succeed – before you know it, you will be celebrating an unexpected milestone.

“When I first went freelance and didn’t have a full calendar of clients yet, I started Desk Life Project as a blog about freelancing and starting a business, to fill my time. I quickly realised that a lot of people are really interested in being self-employed, and want to find out more about how to do it for themselves. The blog went from a few views here and there, to thousands – and since then I’ve added 7 contributing writers to the blog, interviewed many inspiring entrepreneurs about starting their businesses, grown a small but engaged community of freelancers in London helping each other out, and I’m just about to open our online shop this month, which will include resources that help entrepreneurs be more organised and maintain a healthy work-life balance.”

Caitlin McAllister is a freelance writer and founder of Desk Life Project, an online community for freelancers, entrepreneurs and anyone interested in self-employed life. You can follow Caitlin’s journey on Instagram @caitmca, and check out Desk Life Project’s website or Instagram @desklifeproject.

Take The Leap
Jess Levitz – June Letters

“After working for years in the tech industry as an in-house graphic designer, I realised that I was no longer creatively fulfilled or happy working with just one brand in a company environment. I thrive when working from the comforts of home, on short-term projects where I can come in with a bundle of creative energy and then move onto another brand a few months later. When I realised a freelance career was my true goal, I put in many hours after work, blogging, taking on any and every freelance project that came my way, and building my portfolio. I also decided to reach out to a handful of women freelance designers that I admire to ask their advice. They all had wonderful nuggets of wisdom, but one woman in particular said, ‘You will never feel fully ready, you just have to make the leap and you will be ok.’ These were exactly the words I needed to hear to finally put in my notice and fulfill my dream.

“The generosity and honesty of the women I reached out to in those early days led me to create Freelance Wisdom, a website dedicated to sharing the stories and advice of freelance female creatives. We’ve interviewed hundreds of women, and while the advice is diverse, a common thread throughout all the interviews is that creating and sharing the work that you love to do is the best way to reach your dream clients and create a fulfilling career. So thinking of making the leap to a freelance career? Start a personal project and share it with the world. You can do it! Are you a creative lady that could use some support and community? Be sure to follow us on Instagram, ask to join our private Facebook group, and apply to our amazing directory filled with other creative women like you.”

Jess Levitz is the founder of June Letters Studio, a design studio and blog that loves hand-lettering and designing brands. She also created @freelancewisdom, sharing the experiences and know-how of successful female entrepreneurs.

A post shared by Jo Irving (@joloveshair) on

A post shared by Jo Irving (@joloveshair) on

You Are In Charge Of What Happens Next
Jo Irving – Lovehair

“I’ve been working as a bridal hair stylist and entrepreneur since 2000, when I set up my first salon in Scotland. I have had several successful hair businesses, usually started while I was on maternity and always with fire in my belly.

“Being freelance in the hairdressing industry gives me freedom. Financially it’s the most rewarding job I’ve ever had, but it also gives me the luxury to work around my children and never miss a sports day!

“My week is so varied, from working on weddings on a private Island in Indonesia to teaching other stylists the skills they need to go freelance and find their own freedom. I love how much their confidence changes when they finally take the leap. It’s not always easy, but remember: You are 100% in charge of what happens next. I don’t think I would’ve had such variety if I had worked in a salon. I’ve had to make it happen for myself rather than waiting for someone else to promote me. Which is the best bit, I guess!

“The best advice I had was from my brother. He said, ‘Never compare your start to someone else’s middle or end’ – meaning it’s easy to think everyone is doing better than you, but you don’t know what part of their story they’re at. My family members are all self-employed in various careers, so it never crossed my mind to be anything other than my own boss from a really young age.

“Being creative is like no other skill. It gives you the ability to bend and carve your own place in the world, and make money wherever you are. You just need to find your thing. Hair is definitely mine.”

Jo Irving is a hair stylist, entrepreneur and educator based in Surrey, UK, who believes in sexy, cool hair for everyone. Two years ago, she founded the Lovehair Tribe, a stylist support network to help fellow stylists raise their game. Follow Jo on Instagram.

Ask For Help
Becca Booker – According to Bbooks

“I decided I would really go for it in August of 2017, but didn’t actually put in my two weeks at my full-time job until that October!

“The best piece of advice I received was to pretend like it was my full-time job before I would need to rely on it for my income. I set up my business bank account, finalised my social media packages, and tried to line up as many clients as I could – all while I still had a steady paycheck coming in every two weeks.

“If you’re on the cusp of reaching that ‘dream career’, don’t be afraid to ask for help! One of the smartest things I did was hire a therapist who was also a ‘coach’, who I essentially hired to walk me through the process of quitting my job. She was able to offer an unbiased opinion of why I shouldn’t feel guilty about quitting (I worked on a small team) and steps I could take to ensure success before I put in my two weeks!”

Becca Booker is a blogger, social media consultant, Facebook Ad specialist and skincare aficionado. She is the owner of According To Bbooks, a lifestyle blog and social media agency in sunny Scottsdale, Arizona, where she proudly serves her clients with strategic social media campaigns to help them grow their business online. Follow her on Instagram.

A post shared by ashleymateo (@ashleymateo) on

A post shared by ashleymateo (@ashleymateo) on

Hustle, Determination And Thick Skin
Ashley Mateo

“I first went freelance in October 2014, but after two months of travel, a job opportunity came up and I decided to stay in New York. Most recently, in October 2017, I decided to leave my job as the site director at Redbookmag.com in order to travel again.

“The best piece of advice I received was from my dad, when I quit my job for the first time. I wasn’t happy, and I kept complaining about how I should have X title, be working at X publication, be making X salary… His response was that the only thing I ‘should’ be doing is what I wanted to do. And when I thought about that, I realised I really just wanted to travel. It seemed like a big leap to take at the time, but I planned and networked and saved money for a couple of months, and then I did just that.

“I don’t think there’s a such thing as a ‘dream career’. I think your idea of success changes as you change, and you need to be willing to adapt to that. But if you want something – whether that’s a corner office, seed money for a start-up, or the freedom to earn pay checks while traveling the world – no one is going to hand it to you. It takes a lot of hustle, determination and thick skin to go after your goals, but if you put in the work, you’ll eventually find success on your terms, whatever those may be.”

Ashley Mateo is a freelance writer, editor and digital consultant. She is also an avid runner and yogi. Follow her on Instagram.

Never Compare Yourself
Karen D’Arcangelo

“‘If you feel out of your depth and scared when you take on a new project, you’re on the right track. You have to dive in the ocean first in order to learn how to swim.’ This was the best piece of advice I received when I decided to go freelance. It means moving out of your comfort zone and opening up to new adventures and opportunities that are hard to evaluate. It’s easy to bring yourself down and feel like you’re not ‘good enough’ to do a job, so it was helpful to know that the feeling of uncertainty and fear before starting something new is a positive one.

“My advice to people who are just one step away from going freelance is in the words of Nike… ‘Just do it!’ I would definitely recommend having some savings on the side for any emergency, and to be as organised as possible. You’re responsible for your own time and plans, and it’s easy to take on many projects and feel lost and overwhelmed. I recommend having a fairly detailed plan of the week and setting some goals so that you can reach that feeling of accomplishment and productivity we all need.

“Let others inspire and motivate you, but never compare yourself or your work to anyone else. We all work at different paces and in different ways, and other lives always seem more glamorous through the social media lens.”

Karen D’Arcangelo became a brand consultant by following her passion for helping independent businesses, artists and start-ups grow. With a diverse skill set spanning creative strategy, project management and content production, Karen’s consulting style involves finding creative solutions to help entrepreneurs succeed. Follow her on Instagram.


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